Flags of Mystery

In the episode The Menagerie, during Spock's court proceedings, there are two displayed flags flanking Kirk and Mendez.

I got to wondering about these, I've never seen either displayed unfurled, like in a behind the scenes photo. I've read that one is intended to be a political flag and the other to be the Enterprise's flag/emblem. But which is which?

The one on the left kind of looks like the national flag of Cuba.

Anyone have any pictures of these? Where did the props department get them (or make them), are they from some other older show and what do you think they symbolize?

The general consensus is that the red white and blue one is the Cuban flag. However I'm not aware of any pictures of the original props unfurled. If that's the case, any illustrations on the blue and gold flag are conjecture. Best guess is the Enterprise arrowhead or the Starfleet Command Chevron.

The dark blue of the "Cuban" flag nicely matches that used on the background of various UFP flags from the spinoff shows and movies, with the round starfield emblem in the middle. Since the flag is so conveniently (and deliberately) folded, we might postulate it is just the standard UFP flag, turned into a "rank flag" for Commodore Mendez by the addition of a white Commodore stripe going through it. Today's navies mangle their national flags in a similar way by adding stars or other symbols to create rank flags specific to the rank of the visiting flag officer.

The red add-on there need not be part of the actual flag "in reality"; it could be a separate red pennant instead, hanging from the same pole - another practice from various real militaries, although its symbolism for Starfleet is up to us to choose.

(Agreed, tho, that in Desilu reality they apparently just draped the Cuban national flag there. But that's not particularly relevant for the Trek reality.)

The lighter blue flag could well feature the Starfleet Command banana symbol, in both Trek reality and Desilu reality.

It shouldn't be that light, and anyway, the only bit of yellow we see there (apart from the trimming) is more like gold with blue, nonparallel trimmings. There's no national flag like that.

It's quite possible that a special "Starfleet flag" or "Federation flag" was designed and created for the show at this point, and that the Cuban flag was introduced for symmetry and additional decor, forcing TPTB to hide the details of their expensive custom flag as well. And then it so happened that no further opportunities emerged for showing the custom flag in all its glory, and perhaps it was even lost before we got the patriotic scene in "And the Children Shall Lead"...

I seem to recall someone claiming to have read that Bill Theiss made the flags by literally stapling cloth together. It was a quick and dirty job. Maybe this was only the light blue flag and the other was the Cuban flag. Sure looks the part. For my money, I assume the blue flag had the Enterprise delta on it. Though it may well have been the SF Command boomerang. In my personal Star Trek Universe, each ship is part of a larger fleet that is a subdivision of the Starfleet over all. The arrowhead was the symbol for the not just the Enterprise, but the whole sub-fleet. ("Court Martial" would seem to back this up since everyone on the Star Base (except, notably, the actual Starbase staff) wore the same arrowhead as Enterprise even though they were not Enterprise crew.)

What little we see of the center detail of the light blue flag would indeed best match the delta: it tapers much like the witnessed detail, and it's also usually seen outlined in a darker color like the witnessed detail, while the banana isn't.

It's too bad we never got to see this flag spread out. It reappears in "Space Seed", along with the Cuban flag, but it's not folded in a drastically different manner; we can see the symbol is relatively narrow, like the leg or tip of the delta, but it could still be the banana as well.

^Star Trek was a very collaborative production, as I recall. They didn't impose strict segregation of responsibilities; people were free to contribute wherever they could. If they needed a flag in a hurry and Theiss happened to have some spare bits of cloth lying around, I'm sure he would've pitched in. (There was a similar job flexibility in modern Trek, with things like Doug Drexler going from makeup to graphics, visual-effects supervisor Dan Curry contributing his martial-arts expertise, or video playback supervisor Denise Okuda serving as medical consultant.)